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Entry
CA00399                                                            

Classification
Carotenoid Name
2-Hydroxy-β-carotene 5,6-epoxide;
2-Hydroxy-beta-carotene 5,6-epoxide
IUPAC name (2R,5S,6R)-5,6-Epoxy-5,6-dihydro-beta,beta-caroten-2-ol
Formula
C40H56O2
Molecular Weight 
568.848 g/mol
Structure   
Mol file
Carotenoid DB Fingerprints 
Biological functions/Properties 
Number of
conjugated double bonds 
9
Number of
conjugated multiple bonds 
9
Isomers 
InChI
InChI=1S/C40H56O2/c1-30(18-13-20-32(3)23-24-35-34(5)22-15-27-37(35,6)7)16-11-12-17-31(2)19-14-21-33(4)25-29-40-38(8,9)36(41)26-28-39(40,10)42-40/h11-14,16-21,23-25,29,36,41H,15,22,26-28H2,1-10H3/b12-11+,18-13+,19-14+,24-23+,29-25+,30-16+,31-17+,32-20+,33-21+/t36-,39+,40-/m1/s1
InChIKey
CIYCVFPIPRSGLH-FRLLEXNCSA-N
Canonical SMILES
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@]12O[C@@]1(C)CC[C@H](C2(C)C)O)/C)/C)/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C
XLogP
11.849
Hydrogen Bond donors
(Lipinski's definition)
1
Hydrogen Bond Acceptors
(Lipinski's definition)
2
LipinskiFailures
1
Complexity of molecule
0.316
Number of heavy atoms
42
TPSA
(Topological Polar Surface Area) 
32.760 Å2
Source organisms
Trentepohlia iolithus (Ref.51, Ref.53) - Green alga: Ulvophyceae
References
  • Ref.51 : G. Nybraaten, and S. L. Jensen, Acta Chem. Scand. Ser. B, 28,(1974), 483, "Algal Carotenoids. XI. * New Carotenoid Epoxides from Trentepohlia iolithus".
  • Ref.53 : G. Nybraaten, and S. L. Jensen, Acta Chem. Scand. Ser. B, 28,(1974), 485, "Algal Carotenoids. XII. * Chemical Reactions of Carotenoids with 2-Hydroxylated beta-Rings".
  • CAS
    53120-11-9
    Links to other DB
    KNApSAcK: C00022940

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